# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1935397'
loop_
_audit_author_name
_audit_author_address
'Ghodrat Mahmoudi'
;University of Maragheh
Iran
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-09-06 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            'Coordination compound'
_chemical_formula_moiety         'C13 H12 N6 O6 Pb S'
_chemical_formula_sum            'C13 H12 N6 O6 Pb S'
_chemical_formula_iupac          ?
_chemical_formula_weight         587.54

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9203(7)
_cell_length_b                   19.9475(11)
_cell_length_c                   7.7761(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.949(3)
_cell_angle_gamma                90
_cell_volume                     1794.48(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9987
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.38
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.652
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.154
_exptl_crystal_density_diffrn    2.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112

_exptl_absorpt_coefficient_mu    9.563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.06
_exptl_absorpt_correction_T_max  0.32

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            20833
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9

_refine_special_details          
;
;

_reflns_number_total             3161
_reflns_number_gt                2858
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_gt          0.0504
_refine_ls_wR_factor_ref         0.0523
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_number_reflns         3161
_refine_ls_number_parameters     250
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0160P)²+3.6324P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.323
_refine_diff_density_min         -1.343
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.9444(4) 0.3708(2) 0.6064(6) 0.0440(10) Uani d . . . 1 . .
H H1 0.9654 0.4059 0.5421 0.053 Uiso calc U . R 1 . .
C C2 1.0267(4) 0.3270(3) 0.6968(6) 0.0538(12) Uani d . . . 1 . .
H H2 1.1035 0.3325 0.693 0.065 Uiso calc U . R 1 . .
C C3 0.9960(5) 0.2752(3) 0.7930(6) 0.0609(14) Uani d . . . 1 . .
H H3 1.0519 0.2455 0.8535 0.073 Uiso calc U . R 1 . .
C C4 0.8829(5) 0.2676(3) 0.7991(7) 0.0618(14) Uani d . . . 1 . .
H H4 0.8627 0.2328 0.8652 0.074 Uiso calc U . R 1 . .
C C5 0.7988(4) 0.3104(2) 0.7090(6) 0.0490(11) Uani d . . . 1 . .
H H5 0.722 0.3048 0.7132 0.059 Uiso calc U . R 1 . .
C C6 0.8307(4) 0.3624(2) 0.6117(5) 0.0383(9) Uani d . . . 1 . .
C C13 0.1525(5) 0.4684(3) -0.0483(7) 0.0631(14) Uani d . . . 1 . .
H H13 0.1069 0.43 -0.066 0.076 Uiso calc U . R 1 . .
C C12 0.1058(5) 0.5263(3) -0.1278(7) 0.0657(15) Uani d . . . 1 . .
H H12 0.0307 0.527 -0.1982 0.079 Uiso calc U . R 1 . .
C C11 0.1714(5) 0.5833(3) -0.1019(7) 0.0645(14) Uani d . . . 1 . .
H H11 0.1417 0.6235 -0.1543 0.077 Uiso calc U . R 1 . .
C C10 0.2822(4) 0.5802(2) 0.0031(6) 0.0529(12) Uani d . . . 1 . .
H H10 0.3285 0.6183 0.0233 0.064 Uiso calc U . R 1 . .
C C8 0.4397(4) 0.5144(2) 0.1924(5) 0.0405(9) Uani d . . . 1 . .
H H8 0.4842 0.5528 0.2239 0.049 Uiso calc U . R 1 . .
C C9 0.3234(4) 0.5196(2) 0.0777(5) 0.0402(9) Uani d . . . 1 . .
C C7 0.6439(4) 0.3998(2) 0.4186(5) 0.0372(9) Uani d . . . 1 . .
H H2n 0.619(4) 0.4969(12) 0.396(5) 0.045 Uiso d U . D 1 . .
H H1n 0.777(4) 0.4505(12) 0.521(5) 0.045 Uiso d U . D 1 . .
N N1 0.7497(3) 0.41028(17) 0.5206(5) 0.0422(8) Uani d . . D 1 . .
N N2 0.5881(3) 0.45744(17) 0.3598(5) 0.0409(8) Uani d . . D 1 . .
N N3 0.4802(3) 0.45734(16) 0.2493(4) 0.0367(7) Uani d . . . 1 . .
N N4 0.2588(3) 0.46351(18) 0.0523(5) 0.0486(9) Uani d . . . 1 . .
N N5 0.3958(4) 0.3147(2) -0.1763(5) 0.0500(9) Uani d . . . 1 . .
N N6 0.2039(3) 0.41825(17) 0.4288(5) 0.0446(9) Uani d . . . 1 . .
O O1 0.4314(4) 0.36355(19) -0.0786(5) 0.0777(12) Uani d . . . 1 . .
O O3 0.4411(5) 0.3003(2) -0.2960(6) 0.0952(15) Uani d . . . 1 . .
O O2 0.3192(4) 0.2800(2) -0.1419(6) 0.0824(12) Uani d . . . 1 . .
O O4 0.3128(3) 0.42192(16) 0.4598(4) 0.0520(8) Uani d . . . 1 . .
O O5 0.1528(3) 0.37285(19) 0.3358(5) 0.0676(10) Uani d . . . 1 . .
O O6 0.1508(3) 0.46139(17) 0.4905(6) 0.0724(11) Uani d . . . 1 . .
Pb Pb1 0.35439(2) 0.34790(2) 0.19223(2) 0.04096(7) Uani d . . . 1 . .
S S1 0.58769(11) 0.32315(6) 0.36211(18) 0.0523(3) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.373(6) ?
C1 C6 . 1.376(6) ?
C1 H1 . 0.93 ?
C2 C3 . 1.376(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.369(8) ?
C3 H3 . 0.93 ?
C4 C5 . 1.375(7) ?
C4 H4 . 0.93 ?
C5 C6 . 1.390(6) ?
C5 H5 . 0.93 ?
C6 N1 . 1.420(5) ?
C13 N4 . 1.322(6) ?
C13 C12 . 1.365(7) ?
C13 H13 . 0.93 ?
C12 C11 . 1.366(8) ?
C12 H12 . 0.93 ?
C11 C10 . 1.377(7) ?
C11 H11 . 0.93 ?
C10 C9 . 1.379(6) ?
C10 H10 . 0.93 ?
C8 N3 . 1.274(5) ?
C8 C9 . 1.460(6) ?
C8 H8 . 0.93 ?
C9 N4 . 1.345(5) ?
C7 N1 . 1.335(5) ?
C7 N2 . 1.352(5) ?
C7 S1 . 1.685(4) ?
N1 H1n . 0.865(19) ?
N2 N3 . 1.364(5) ?
N2 H2n . 0.884(14) ?
N3 Pb1 . 2.625(3) ?
N4 Pb1 . 2.684(4) ?
N5 O3 . 1.218(5) ?
N5 O2 . 1.226(5) ?
N5 O1 . 1.245(5) ?
N6 O5 . 1.225(5) ?
N6 O6 . 1.231(5) ?
N6 O4 . 1.264(5) ?
O1 Pb1 . 2.511(4) ?
O4 Pb1 . 2.693(3) ?
Pb1 S1 . 2.8199(13) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.6(4) ?
C2 C1 H1 . . 120.2 ?
C6 C1 H1 . . 120.2 ?
C1 C2 C3 . . 120.4(5) ?
C1 C2 H2 . . 119.8 ?
C3 C2 H2 . . 119.8 ?
C4 C3 C2 . . 119.7(5) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 121.1(5) ?
C3 C4 H4 . . 119.4 ?
C5 C4 H4 . . 119.4 ?
C4 C5 C6 . . 118.7(5) ?
C4 C5 H5 . . 120.7 ?
C6 C5 H5 . . 120.7 ?
C1 C6 C5 . . 120.5(4) ?
C1 C6 N1 . . 117.4(4) ?
C5 C6 N1 . . 122.1(4) ?
N4 C13 C12 . . 124.0(5) ?
N4 C13 H13 . . 118.0 ?
C12 C13 H13 . . 118.0 ?
C13 C12 C11 . . 118.7(5) ?
C13 C12 H12 . . 120.6 ?
C11 C12 H12 . . 120.6 ?
C12 C11 C10 . . 118.9(5) ?
C12 C11 H11 . . 120.5 ?
C10 C11 H11 . . 120.5 ?
C11 C10 C9 . . 118.9(5) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
N3 C8 C9 . . 120.0(4) ?
N3 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
N4 C9 C10 . . 122.3(4) ?
N4 C9 C8 . . 117.2(4) ?
C10 C9 C8 . . 120.5(4) ?
N1 C7 N2 . . 112.7(4) ?
N1 C7 S1 . . 123.8(3) ?
N2 C7 S1 . . 123.4(3) ?
C7 N1 C6 . . 128.5(4) ?
C7 N1 H1n . . 116.(3) ?
C6 N1 H1n . . 115.(3) ?
C7 N2 N3 . . 121.6(3) ?
C7 N2 H2n . . 121.(3) ?
N3 N2 H2n . . 117.(3) ?
C8 N3 N2 . . 116.0(3) ?
C8 N3 Pb1 . . 122.1(3) ?
N2 N3 Pb1 . . 121.4(2) ?
C13 N4 C9 . . 117.3(4) ?
C13 N4 Pb1 . . 123.8(3) ?
C9 N4 Pb1 . . 118.9(3) ?
O3 N5 O2 . . 121.6(5) ?
O3 N5 O1 . . 120.2(5) ?
O2 N5 O1 . . 118.1(4) ?
O5 N6 O6 . . 121.2(4) ?
O5 N6 O4 . . 119.8(4) ?
O6 N6 O4 . . 119.0(4) ?
N5 O1 Pb1 . . 105.9(3) ?
N6 O4 Pb1 . . 101.1(2) ?
O1 Pb1 N3 . . 74.27(11) ?
O1 Pb1 N4 . . 76.03(13) ?
N3 Pb1 N4 . . 61.53(11) ?
O1 Pb1 O4 . . 138.80(11) ?
N3 Pb1 O4 . . 67.52(10) ?
N4 Pb1 O4 . . 72.71(11) ?
O1 Pb1 S1 . . 84.04(12) ?
N3 Pb1 S1 . . 66.91(8) ?
N4 Pb1 S1 . . 127.94(8) ?
O4 Pb1 S1 . . 94.51(7) ?
C7 S1 Pb1 . . 104.41(15) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.3(7) ?
C1 C2 C3 C4 . . . . -0.3(7) ?
C2 C3 C4 C5 . . . . 0.7(8) ?
C3 C4 C5 C6 . . . . -0.4(7) ?
C2 C1 C6 C5 . . . . 0.6(6) ?
C2 C1 C6 N1 . . . . 178.1(4) ?
C4 C5 C6 C1 . . . . -0.3(7) ?
C4 C5 C6 N1 . . . . -177.6(4) ?
N4 C13 C12 C11 . . . . -0.5(9) ?
C13 C12 C11 C10 . . . . 0.1(8) ?
C12 C11 C10 C9 . . . . 0.3(8) ?
C11 C10 C9 N4 . . . . -0.4(7) ?
C11 C10 C9 C8 . . . . -178.9(4) ?
N3 C8 C9 N4 . . . . 7.0(6) ?
N3 C8 C9 C10 . . . . -174.4(4) ?
N2 C7 N1 C6 . . . . 176.8(4) ?
S1 C7 N1 C6 . . . . -5.5(6) ?
C1 C6 N1 C7 . . . . 137.4(4) ?
C5 C6 N1 C7 . . . . -45.2(6) ?
N1 C7 N2 N3 . . . . 178.0(3) ?
S1 C7 N2 N3 . . . . 0.3(6) ?
C9 C8 N3 N2 . . . . -178.1(3) ?
C9 C8 N3 Pb1 . . . . -5.9(5) ?
C7 N2 N3 C8 . . . . -175.1(4) ?
C7 N2 N3 Pb1 . . . . 12.6(5) ?
C12 C13 N4 C9 . . . . 0.5(8) ?
C12 C13 N4 Pb1 . . . . -176.2(4) ?
C10 C9 N4 C13 . . . . 0.0(7) ?
C8 C9 N4 C13 . . . . 178.5(4) ?
C10 C9 N4 Pb1 . . . . 176.8(3) ?
C8 C9 N4 Pb1 . . . . -4.6(5) ?
O3 N5 O1 Pb1 . . . . -162.5(4) ?
O2 N5 O1 Pb1 . . . . 13.6(5) ?
O5 N6 O4 Pb1 . . . . 20.2(4) ?
O6 N6 O4 Pb1 . . . . -158.4(3) ?
N1 C7 S1 Pb1 . . . . 171.9(3) ?
N2 C7 S1 Pb1 . . . . -10.7(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C1 H1 O6 1_655 0.93 2.59 3.347(6) 139.2 ?
C8 H8 O1 3_665 0.93 2.37 3.118(5) 137.2 ?
N2 H2n O4 3_666 0.884(14) 2.026(18) 2.891(5) 166.(4) ?
N1 H1n N6 3_666 0.865(19) 2.65(2) 3.472(5) 159.(4) ?
N1 H1n O6 3_666 0.865(19) 1.97(2) 2.831(5) 175.(4) ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1935400'
loop_
_audit_author_name
_audit_author_address
'Ghodrat Mahmoudi'
;University of Maragheh
Iran
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-09-06 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            'Coordination Compound'
_chemical_formula_moiety         '	C19 H15 N5 O3 Pb S'
_chemical_formula_sum            'C19 H15 N5 O3 Pb S'
_chemical_formula_iupac          ?
_chemical_formula_weight         600.61

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   37.250(5)
_cell_length_b                   5.0731(6)
_cell_length_c                   22.594(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.797(14)
_cell_angle_gamma                90
_cell_volume                     3991.5(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9488
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.42
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2288

_exptl_absorpt_coefficient_mu    8.590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_T_max  0.67

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            33393
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_full        27.11
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             4416
_reflns_number_gt                3820
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0582
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         4416
_refine_ls_number_parameters     265
_refine_ls_number_restraints     7
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0187P)²+12.4262P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.165
_refine_diff_density_min         -1.390
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2014.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXTL V6.14 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL V6.14 (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.38125(12) 1.0883(8) 0.6654(2) 0.0371(10) Uani d . . . 1 . .
C C2 0.38624(14) 1.2750(10) 0.7127(2) 0.0522(12) Uani d . . . 1 . .
H H2 0.3673 1.4003 0.7085 0.063 Uiso calc U . R 1 . .
C C3 0.41914(17) 1.2748(12) 0.7656(3) 0.0677(15) Uani d . . . 1 . .
H H3A 0.422 1.3996 0.7972 0.081 Uiso calc U . R 1 . .
C C4 0.44742(16) 1.0958(11) 0.7727(3) 0.0667(16) Uani d . . . 1 . .
H H4 0.4697 1.0987 0.8085 0.08 Uiso calc U . R 1 . .
C C5 0.44287(16) 0.9127(11) 0.7269(3) 0.0670(16) Uani d . . . 1 . .
H H5 0.4622 0.79 0.7314 0.08 Uiso calc U . R 1 . .
C C6 0.40943(14) 0.9056(9) 0.6730(2) 0.0544(13) Uani d . . . 1 . .
H H6 0.4064 0.7767 0.6423 0.065 Uiso calc U . R 1 . .
C C7 0.33532(11) 0.9714(8) 0.55680(19) 0.0336(9) Uani d . . . 1 . .
C C8 0.37050(12) 0.5770(7) 0.4690(2) 0.0363(9) Uani d . . . 1 . .
C C9 0.41194(12) 0.5670(8) 0.5094(2) 0.0402(10) Uani d U . . 1 . .
C C10 0.43825(17) 0.7243(14) 0.4993(4) 0.101(3) Uani d . . . 1 . .
H H10 0.4309 0.8368 0.4645 0.121 Uiso calc U . R 1 . .
C C11 0.47661(19) 0.7201(17) 0.5407(5) 0.137(4) Uani d . . . 1 . .
H H11 0.4946 0.8303 0.5335 0.164 Uiso calc U . R 1 . .
C C12 0.48749(19) 0.5566(14) 0.5910(4) 0.092(2) Uani d . . . 1 . .
H H12 0.5129 0.5543 0.6187 0.111 Uiso calc U . R 1 . .
C C13 0.46184(17) 0.4001(15) 0.6005(3) 0.090(2) Uani d . . . 1 . .
H H13 0.4693 0.2858 0.635 0.109 Uiso calc U . R 1 . .
C C14 0.42414(15) 0.4036(12) 0.5603(3) 0.0774(19) Uani d U . . 1 . .
H H14 0.4066 0.2913 0.5681 0.093 Uiso calc U . R 1 . .
C C15 0.35688(12) 0.4534(8) 0.4059(2) 0.0391(10) Uani d . . . 1 . .
C C16 0.38060(15) 0.3085(10) 0.3834(2) 0.0576(13) Uani d . . . 1 . .
H H16 0.4063 0.2842 0.4084 0.069 Uiso calc U . R 1 . .
C C17 0.36604(18) 0.1998(12) 0.3238(3) 0.0736(17) Uani d . . . 1 . .
H H17 0.3818 0.1005 0.3084 0.088 Uiso calc U . R 1 . .
C C18 0.32824(17) 0.2389(11) 0.2873(3) 0.0636(14) Uani d . . . 1 . .
H H18 0.3181 0.1704 0.2466 0.076 Uiso calc U . R 1 . .
C C19 0.30569(15) 0.3804(10) 0.3120(2) 0.0537(12) Uani d . . . 1 . .
H H19 0.2798 0.4029 0.2878 0.064 Uiso calc U . R 1 . .
H H1N 0.3302(12) 1.216(8) 0.616(2) 0.064 Uiso d U . D 1 . .
N N1 0.34645(10) 1.1009(7) 0.61279(17) 0.0402(8) Uani d . . D 1 . .
N N2 0.35934(9) 0.8106(7) 0.54571(16) 0.0408(8) Uani d . . . 1 . .
N N3 0.34524(9) 0.6917(7) 0.48713(16) 0.0387(8) Uani d . . . 1 . .
N N5 0.22670(11) 1.0595(7) 0.34616(17) 0.0403(9) Uani d . . . 1 . .
N N4 0.31960(10) 0.4881(8) 0.37007(17) 0.0440(9) Uani d . . . 1 . .
O O1 0.25587(10) 0.9491(7) 0.34172(16) 0.0540(8) Uani d . . . 1 . .
O O2 0.20938(9) 0.9504(7) 0.37693(17) 0.0551(9) Uani d . . . 1 . .
O O3 0.21629(11) 1.2734(7) 0.32100(19) 0.0713(11) Uani d . . . 1 . .
Pb Pb1 0.27423(2) 0.61190(3) 0.42859(2) 0.03445(6) Uani d . . . 1 . .
S S1 0.28907(3) 1.0551(2) 0.50497(5) 0.0362(2) Uani d . . . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.365(6) ?
C1 C2 . 1.390(6) ?
C1 N1 . 1.416(5) ?
C2 C3 . 1.375(7) ?
C2 H2 . 0.93 ?
C3 C4 . 1.357(8) ?
C3 H3A . 0.93 ?
C4 C5 . 1.355(8) ?
C4 H4 . 0.93 ?
C5 C6 . 1.401(7) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C7 N2 . 1.299(5) ?
C7 N1 . 1.353(5) ?
C7 S1 . 1.757(4) ?
C8 N3 . 1.290(5) ?
C8 C15 . 1.472(6) ?
C8 C9 . 1.489(6) ?
C9 C10 . 1.345(7) ?
C9 C14 . 1.357(7) ?
C10 C11 . 1.403(9) ?
C10 H10 . 0.93 ?
C11 C12 . 1.347(11) ?
C11 H11 . 0.93 ?
C12 C13 . 1.318(9) ?
C12 H12 . 0.93 ?
C13 C14 . 1.376(8) ?
C13 H13 . 0.93 ?
C14 H14 . 0.93 ?
C15 N4 . 1.348(5) ?
C15 C16 . 1.378(6) ?
C16 C17 . 1.376(7) ?
C16 H16 . 0.93 ?
C17 C18 . 1.370(8) ?
C17 H17 . 0.93 ?
C18 C19 . 1.365(7) ?
C18 H18 . 0.93 ?
C19 N4 . 1.344(6) ?
C19 H19 . 0.93 ?
N1 H1N . 0.863(19) ?
N2 N3 . 1.378(5) ?
N3 Pb1 . 2.535(3) ?
N5 O3 . 1.222(5) ?
N5 O2 . 1.235(5) ?
N5 O1 . 1.258(5) ?
N4 Pb1 . 2.566(4) ?
O1 Pb1 . 2.509(3) ?
Pb1 S1 . 2.7681(11) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 118.7(4) ?
C6 C1 N1 . . 124.7(4) ?
C2 C1 N1 . . 116.6(4) ?
C3 C2 C1 . . 120.2(5) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?
C4 C3 C2 . . 121.1(5) ?
C4 C3 H3A . . 119.4 ?
C2 C3 H3A . . 119.4 ?
C5 C4 C3 . . 119.2(5) ?
C5 C4 H4 . . 120.4 ?
C3 C4 H4 . . 120.4 ?
C4 C5 C6 . . 120.9(5) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C1 C6 C5 . . 119.9(5) ?
C1 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
N2 C7 N1 . . 118.8(4) ?
N2 C7 S1 . . 127.0(3) ?
N1 C7 S1 . . 114.1(3) ?
N3 C8 C15 . . 117.3(4) ?
N3 C8 C9 . . 122.3(4) ?
C15 C8 C9 . . 120.3(4) ?
C10 C9 C14 . . 117.5(5) ?
C10 C9 C8 . . 122.3(4) ?
C14 C9 C8 . . 120.2(4) ?
C9 C10 C11 . . 120.6(6) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C12 C11 C10 . . 120.1(7) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C13 C12 C11 . . 119.4(6) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.9(6) ?
C12 C13 H13 . . 119.6 ?
C14 C13 H13 . . 119.6 ?
C9 C14 C13 . . 121.6(6) ?
C9 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
N4 C15 C16 . . 120.4(4) ?
N4 C15 C8 . . 117.0(4) ?
C16 C15 C8 . . 122.6(4) ?
C17 C16 C15 . . 119.6(5) ?
C17 C16 H16 . . 120.2 ?
C15 C16 H16 . . 120.2 ?
C18 C17 C16 . . 119.6(5) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C19 C18 C17 . . 118.7(5) ?
C19 C18 H18 . . 120.6 ?
C17 C18 H18 . . 120.6 ?
N4 C19 C18 . . 122.2(5) ?
N4 C19 H19 . . 118.9 ?
C18 C19 H19 . . 118.9 ?
C7 N1 C1 . . 130.4(4) ?
C7 N1 H1N . . 115.(3) ?
C1 N1 H1N . . 115.(3) ?
C7 N2 N3 . . 114.0(3) ?
C8 N3 N2 . . 115.5(3) ?
C8 N3 Pb1 . . 120.4(3) ?
N2 N3 Pb1 . . 122.9(2) ?
O3 N5 O2 . . 121.1(4) ?
O3 N5 O1 . . 119.9(4) ?
O2 N5 O1 . . 118.9(3) ?
C19 N4 C15 . . 119.4(4) ?
C19 N4 Pb1 . . 120.4(3) ?
C15 N4 Pb1 . . 116.7(3) ?
N5 O1 Pb1 . . 104.2(3) ?
O1 Pb1 N3 . . 104.10(12) ?
O1 Pb1 N4 . . 79.06(11) ?
N3 Pb1 N4 . . 63.38(11) ?
O1 Pb1 S1 . . 82.67(9) ?
N3 Pb1 S1 . . 66.71(8) ?
N4 Pb1 S1 . . 119.85(9) ?
C7 S1 Pb1 . . 98.67(14) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.4(7) ?
N1 C1 C2 C3 . . . . 179.5(5) ?
C1 C2 C3 C4 . . . . 0.6(9) ?
C2 C3 C4 C5 . . . . -0.7(9) ?
C3 C4 C5 C6 . . . . -0.3(9) ?
C2 C1 C6 C5 . . . . -1.3(7) ?
N1 C1 C6 C5 . . . . 179.7(5) ?
C4 C5 C6 C1 . . . . 1.3(9) ?
N3 C8 C9 C10 . . . . -102.8(7) ?
C15 C8 C9 C10 . . . . 77.3(7) ?
N3 C8 C9 C14 . . . . 74.2(6) ?
C15 C8 C9 C14 . . . . -105.7(6) ?
C14 C9 C10 C11 . . . . -1.0(11) ?
C8 C9 C10 C11 . . . . 176.1(7) ?
C9 C10 C11 C12 . . . . 0.4(15) ?
C10 C11 C12 C13 . . . . 0.5(15) ?
C11 C12 C13 C14 . . . . -0.7(13) ?
C10 C9 C14 C13 . . . . 0.8(10) ?
C8 C9 C14 C13 . . . . -176.4(6) ?
C12 C13 C14 C9 . . . . 0.1(12) ?
N3 C8 C15 N4 . . . . 5.2(6) ?
C9 C8 C15 N4 . . . . -174.9(4) ?
N3 C8 C15 C16 . . . . -175.0(5) ?
C9 C8 C15 C16 . . . . 4.9(7) ?
N4 C15 C16 C17 . . . . 0.3(8) ?
C8 C15 C16 C17 . . . . -179.5(5) ?
C15 C16 C17 C18 . . . . 0.5(9) ?
C16 C17 C18 C19 . . . . -1.6(9) ?
C17 C18 C19 N4 . . . . 1.8(8) ?
N2 C7 N1 C1 . . . . -1.8(7) ?
S1 C7 N1 C1 . . . . -179.3(3) ?
C6 C1 N1 C7 . . . . -10.1(7) ?
C2 C1 N1 C7 . . . . 170.8(4) ?
N1 C7 N2 N3 . . . . -179.3(4) ?
S1 C7 N2 N3 . . . . -2.1(6) ?
C15 C8 N3 N2 . . . . -178.4(3) ?
C9 C8 N3 N2 . . . . 1.7(6) ?
C15 C8 N3 Pb1 . . . . 14.2(5) ?
C9 C8 N3 Pb1 . . . . -165.7(3) ?
C7 N2 N3 C8 . . . . 165.6(4) ?
C7 N2 N3 Pb1 . . . . -27.3(5) ?
C18 C19 N4 C15 . . . . -1.0(7) ?
C18 C19 N4 Pb1 . . . . -159.3(4) ?
C16 C15 N4 C19 . . . . -0.1(7) ?
C8 C15 N4 C19 . . . . 179.8(4) ?
C16 C15 N4 Pb1 . . . . 159.0(4) ?
C8 C15 N4 Pb1 . . . . -21.2(5) ?
O3 N5 O1 Pb1 . . . . 162.2(3) ?
O2 N5 O1 Pb1 . . . . -16.6(4) ?
N2 C7 S1 Pb1 . . . . 23.7(4) ?
N1 C7 S1 Pb1 . . . . -159.0(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C6 H6 N2 . 0.93 2.27 2.858(6) 120.7 ?
C18 H18 O3 4_535 0.93 2.58 3.382(6) 145.1 ?
N1 H1N O2 7_576 0.863(19) 2.29(2) 3.147(5) 175.(5) ?
N1 H1N O3 7_576 0.863(19) 2.60(4) 3.254(5) 133.(4) ?

